Tempo → HCID 58055098, compound

Participants

Reaction Steps

Crude (R)-(5-methyltetrahydrofuran-2-yl)methanol was dissolved in 6 mL of 1:1 ACN/water mixture, and bis-acetoxyiodobenzene [BAIB] (0.71 g, 2.20 mmol) was added to the mixture. It was then cooled to 0 C in an ice bath, and TEMPO (0.031 g, 0.2 mmol) was added under argon flow. The mixture was stirred at room temperature for 3 h, and the reaction was quenched by addition of 20 mL of 1 M NaOH. Basic solution was washed 3×15 mL of EtOAc, and re-acidified with 1 M HCl to ca. pH 2. Aqueous layer was then extracted 6×15 mL of EtOAc, organic layers combined, dried over sodium sulfate and evaporated. Resulting oil (0.05 g, 26%) was used in the next step with no purification. 1H NMR (300 MHz, CDCl3) δ 4.48-4.43 (m, 1H), 4.20-4.17 (m, 1H), 2.33-2.21 (m, 3H), 2.08-2.02 (m, 1H), 1.35 (dd, 3H, J1=6.3 Hz, J2=1.8 Hz).

Provenance & Evidence